The Insurrectionists
by WaywardSun
Summary: AU political thriller. John Winchester, leader of the Insurrectionists, is arrested by his own party and executed after pleading guilty. Castiel Novak, his best friend and new leader of the party, was the one who had to turn him in. Now he suspects that Lucifer, leader of the Opportunists, set them all up in order to silence John and condemn his sons to a life of indentured service
1. PROLOGUE

**PROLOGUE**

 **MARCH 23, 1995**

 **MOJAVE** **FEDERAL PRISON, CALIFORNIA**

"Jesus Christ, John," muttered Bobby as he plopped down on the other side of the visitor's booth, slapping down a thick file folder onto the counter. "What a bloody mess you've gotten yourself into."

"Bobby?" John queried in disbelief as he squinted his eyes, reached forward, and hooked his fingers into the wire partition that was separating them. "Is that….is that you?"

"In the flesh. Been a long time." Ten years, actually.

"Holy shit. What...how... _what in the hell are you doing here_?" he nearly screeched.

"I asked to be here. Calm down, let's talk like gentlemen. It's just you and me. Nothing's being recorded, and we only have one chance to speak."

John was so taken aback that he literally could not get the mechanisms in his throat to work in order to enable to him to respond - had he anything to say, that is. For now, all he could do was stare and gape. So Bobby dived right in.

"Lucifer has appointed me as the negotiator for this discussion, prior to the arraignment tomorrow. You do know that's happening tomorrow, right? I don't know what they've told you."

John continued to stare, and Bobby gave it right back to him. Several long moments passed.

"What. _the hell_. are you doing. _here_ ," John repeated, having almost recovered from the shock. There was no anger in the question, although there should be, considering what happened the last time they saw each other.

"As I said," Bobby repeated calmly, although he felt like passing out from anxiety, "I'm a pre-arraignment negotiator. Appointed by Lucifer himself. We only have one hour, John. Shall we get to it?"

John stood up and walked away, pacing his little booth fruitlessly, hoping to exit. There was no guard to let him out, though, and after pounding on the door a few times without response, he stood against the back wall as far as he could go, glaring daggers at his former friend.

"Yes, I know the arraignment is tomorrow, to answer your question. But this makes absolutely zero sense. The Opportunists aren't the ones bringing charges against me, and you're not a government official, so why the hell does Lucifer have any right to appoint anybody for this trial? I repeat: _why are you here_?"

"Because we are involved as an interested party for the corporate espionage charges. But never mind that, I don't have time to explain the law. I'm actually here to talk about Sam and Dean...more specifically, to discuss their future if you are found guilty. You should know that Lucifer is aware of my previous relationship with you, and how much I love the boys, too. That's why he thought my presence would be better than someone who doesn't understand the depth of their attachment to you, and vice versa."

John said nothing.

"Are you going to talk to me, or just stare at me like I have three heads?" Bobby asked harshly. "Sit down, John."

"If this is prelude to a grave threat against my sons, I'm happy to stand here and stare at you for 54 more minutes, because that's all you're going to get."

"Actually, it's not a threat. I'm here to help."

John snorted. "Right. Help. What do you want, exactly?"

"To be precise, I want you to sit down in front of me and talk about old times for a few minutes. Then we will talk about the future. There will be no more arguing from my end, but you're welcome to it if it makes you feel better. Just don't expect me to reciprocate. Please sit, John."

Bobby watched as John gauged his expression critically, then crossed the room and sat down heavily. He smiled sardonically and pitched his tone up to an excessively cheerful tenor.

"So, Bobby, old friend. How have you been? Life treating you well? Divorced yet? Got kids? Been on vacation? Do tell."

Bobby sighed. "Fine. Not really. Widower. No kids. No vacation. Anything else?"

"Not for the moment," John replied in a normal tone, feeling like a total shit suddenly. "I'm very sorry to hear about Karen."

"Thank you. Let's proceed. Listen, John. These charges...if you plead not guilty against the evidence, the trial is going to be an absolute shit show. Even without it, you must know the jury will be heavily prejudiced against you, especially with your recent tirade against your own constituents."

"It wasn't a tirade, it was a...forget that! I thought you were only here to discuss the boys," John replied sharply, pounding the counter as he did so.

"In a minute." He picked up the file. "Bribery of state officials. Abuse of the public trust. Political espionage...that's the one that allows Lucifer in the game. Treason against the nation. I'm not here to discuss your guilt or innocence, but-"

"I won't be found guilty," John responded confidently. "These charges were only brought three days ago, but-"

"Yes, you will. That's why I'm here."

Now John looked at him like he really _did_ have three heads. "What are you saying?"

Bobby took a deep breath and lowered his voice. "I'm saying...look, it's really difficult to say this to you, but I have to. John, this is so bad that _your own party_ decided to lock you up, not us. This is their doing. I'm not the enemy. Lucifer's not the enemy, at least not right now. I'm just wondering how the hell it was _you_ that finally brought down the Insurrectionists? I mean, perhaps I should be saying thank you, but damn, I'm just as confused as everyone else. This is unprecedented. It's sensational."

"If you are already convinced of my guilt, why are you here?" John demanded furiously. "Lucifer should be doing handstands and throwing a party right about now. Not trying to help my sons. None of this makes sense, and I would appreciate if you would get to the point."

Bobby's eyes narrowed. "Again, I'm here to talk about what's going to happen to Sam and Dean if you are found guilty by a jury."

John grinned. "I can still read you like a book after all these years, Bobby. You're threatening my sons because a trial could prompt me to expose things that would bring down Lucifer, should I decide to bargain with the government instead of you. This is such an obvious ploy that I'm almost disappointed at the lack of suspense."

Bobby hesitated for the first time, and felt unsure of his own footing for a few moments. John wasn't wrong to be angry about the party's motives where he was concerned, but no one was threatening the boys. Bobby would never have agreed to such a tactic, and neither would Lucifer - who, after all, was the one trying so hard to change the current law regarding what happens to the orphans of convicted felons.

"Alright, John. Let's put emotions aside and talk facts instead for the moment. If you are found guilty by trial, your boys will be deeded to the state for life. And that's whether you spend 48 hours or 48 years in jail. It's automatic, no negotiation. You know that already, I assume?"

John nodded wordlessly. He was pale and sweaty all of a sudden.

Bobby softened his tone, hating himself for what he had to say next. "The Opportunists can propose a plea deal in which that does not occur, but you must plead guilty and agree to immediate execution. Before you decide, I'll remind you one last time that your conviction is certain."

John's expression could have set the world on fire in its intensity. He leaned forward, thankful for the wire barricade that would stop him from adding homicide to the long list of charges against him.

"You son of a bitch," he growled dangerously. "Now I see why our conversation isn't being recorded."

CONTINUED IN NEXT CHAPTER


	2. The Call

**[PLEASE NOTE: THIS CHAPTER TAKES PLACE 4 MONTHS *BEFORE* THE LAST CHAPTER]**

 **December 1994**

 **Insurrectionists HQ, Los Angeles**

It was 9pm, and Castiel hadn't even sifted through half of his newfangled "email" for the day yet. It seemed like for every one he answered, two more would appear in his box to take its place. How was this technology supposed to make life easier? All it did was create more work in a shorter timespan.

The desk phone rang; he leaned over to press the speakerphone button and dumped half a cup of espresso into his lap at the same time.

"Fuck. Yes, boss?"

"Not right now, honey, I have a headache," John retorted with a snort.

"Sorry to hear that. I have ibuprofen and Aleve."

John rolled his eyes and sighed. "Hey, call it a night already, would you? Your office light is keeping me awake down here."

Castiel leaned all the over his desk and looked out the door down the hallway. John was doing the same from his office, but the lights were off.

"You're sleeping in the office? Did something happen at the house?"

There was a bark of laughter from the dark office. "No, I'm actually heading out. Sam isn't feeling well. Hang up, I'm coming over."

John gathered up his coat and briefcase and strolled into Castiel's office.

"Look, I know you don't celebrate Christmas and all, but I wish you'd reconsider for once. Tomorrow night's going to be a hell of a party."

Castiel dabbed feverishly at his slacks with a comically large stack of cocktail napkins. "I'm not sure I would enjoy a party described as hellish, John. Please forgive me for passing it up."

 **Winchester Manor, Christmas Eve 1994**

Castiel went to the party, of course. He wasn't nearly as immune to his boss's charms as he wished he could be; the man could get literally anyone to do anything he wanted. That's why he made a perfect party leader, after all.

After giving his coat to a house boy and heading to the bar for a glass of water, his phone rang noisily.

 _Unknown number._

Castiel never answered unknown numbers, and he proceeded to ignore it the next five times it rang with a call as well. On the seventh time, however, his curiosity got the best of him and he pulled it back out of his pocket and decided to answer. Since his voice as the speaker of the party was so well-known and constantly mimicked, he pitched it up a bit to avoid the caller identifying the number as his.

"Yes?" he answered. "Who is calling?"

"Do you have a moment to speak in private, Castiel? It's important."

Castiel moved outside to a quiet corner of the patio, interest now greatly piqued. "I think you have the wrong number," he tried hopefully. "But if you tell me what it's about, maybe I can point you in the right direction."

"I am calling on the emergency line with some information that you personally need to hear. Immediately. And I know this is Castiel, so please don't keep pretending I have the wrong number."

Castiel's blood went cold. That's why the caller got directed to this phone; the emergency number that was given to all undercover agents was diverted to an unlisted office line, which was currently forwarded to his cell. He had never actually received one of these calls before.

"I'm listening. Please proceed."

"Only if you promise to look in this immediately. I'm risking everything to call you right now. But I trust you with my life to do what you'll say you'll do."

"I promise I will address it immediately. Tell me what's going on."

"Political treason, Castiel, plain and simple. Four days ago John Winchester paid a leader of the Opportunists to plant an agent within the government, who would be working on behalf of Lucifer. The reason I know this is because I happen to be the particular agent that's been chosen for the task. The problem is, I already work for you guys. For us, rather. So I'm bugging out, and I'll need you to send me relocation and restart compensation. Without getting John involved, obviously."

 _Holy shit._

Castiel cleared his throat and tried to sound unconcerned. "Look, I know you have a verification code that can prove your identity, but I'm not in my office and can't cross-check it. You'll either have to wait until I can get there in about half an hour, or call me back tomorrow at 8am Pacific, okay? Don't say anything else until then."

"Has to be tomorrow. They're making my arrangements now to leave for the Capital and I'll go, but somehow on the way there-"

"I can't say anything more until you're verified. I have to end this call now. You must call me tomorrow at 8am and no later. Be careful."

He disconnected the call and carefully set his face expressionless as John approached him and offered a glass of champagne, which Castiel relectuantly took.

"Merry Christmas, Cas. You're standing under the mistletoe, so that means I get to kiss you now. Always wanted to do that, actually," he joked easily. A little alcohol always loosened him up enough to flirt with just about anybody.

Castiel ignored this tiresome banter. "Can we go somewhere private for a few minutes?"

"Oooh, moving so fast. I hope we'll be doing more than talking," John teased again, although there was absolutely nothing meant by it other than to make his subordinate blush.

"I'm serious, boss. I just received an emergency call that you need to know about immediately."

That sorted John out; he led the way to his first floor library, far from the opposite wing of the house where the party was taking place.

John was no longer interested in his wine and set it down on the sideboard as he closed the door.

"What's up, Cas? You've got my adrenaline going, so let's hear it."

"The Opportunists are about to make one of our agents. I don't know who he is yet, but he's going to call me back."

"Well, shit. Get Charlie to start the relocation process, then. That's unfortunate. What exactly did he say?"

Castiel took a deep breath and tried not to let his nervousness show.

"He said...well, it was about a meeting you had on Tuesday. He is deeply concerned that you were misled about the man's identity and motives. Seems the outcome of that meeting was this agent being chosen for a mission for the Opportunists which he cannot undertake or decline without being exposed."

It wasn't the whole truth... but it wasn't a lie, either.

"Jesus," John breathed heavily. "I had five or six meetings that day. Did he say which one?"

"No." Here goes nothing, Castiel thought. "But if you get me a list of who you met with, I'll look into them immediately. We should be able to pin it down quickly."

John looked a little startled. "Did you verify this agent's identity?"

"Uh, no. Not yet."

John looked annoyed. "Oh come on Cas, you know better than to talk to unverified callers on that line! Do that first, and then I'll get you the list. For all we know, he was captured and is calling under duress. The code he gives will tell us."

"But we should get started right away-"

"No. There's also the possibility he got cold feet and wants to disappear on our dime. When's he going to call back?"

Castiel had never lied to John before - even when he probably should have - and wasn't about to start now. "Tomorrow at 8am."

"Christmas day? Nice."

"John, don't you think it's best if we start to check up on those names right now? Why wait?"

"Cas, I think we should enjoy this party. It's Christmas eve. Come on."

Despite John's casual dismissal of the need for urgent action, he seemed unnerved as he swept his wine off the sideboard and disappeared without another glance at his colleague and friend. Castiel watched him go, his heart suddenly heavy with uncertainty. If John insisted on joining him to hear the agent's call, things were about to get very complicated.

Merry Christmas, indeed...

 **CONTINUED IN NEXT CHAPTER**


	3. Castiel's Conundrum

**Christmas Day, 1994**

 **Insurrectionists HQ, Los Angeles**

Castiel arrived at the office at 7am, eager to hear back from the agent regarding the intel he had passed along during John's Christmas party. First things first - he had to identify the agent. There were five individualized codes that the man had to memorize upon his first day of work, and each of them had a separate purpose to be used to calls to their superiors or the emergency line:

1 - agent reporting normally

2 - agent reporting under duress, information is accurate

3 - agent reporting under duress, information is false

4 - agent is made, attempt a rescue

5 - agent is made, do not attempt rescue

Depending on what code the man gave, Cas would know the situation immediately and be able to act accordingly. His predecessor had been the one to take these calls; this was his first, and the anxiety was almost unbearable for several reasons.

Obviously, the first reason was because of the reason for the call. Number 3 in this case would be the best scenario in regards to what he had said about John. Number 1 would be the worst case.

Then, there was the problem about him having honestly told John the time that the agent was going to be calling. He wished he had lied. As a preventative measure, he had pulled Gabriel aside at the Christmas party and asked him to help get John as drunk as possible. The man's hangovers were few but epic, and if anything could prevent him from showing up at the office at 8am, that would be the thing to do it. Gabriel hadn't asked questions, and Castiel watched him bring glass after glass to their boss.

The last thing causing him such anxiety was the idea that he might have to go behind John's back to get the full story, and that was the worst part. In ten years they had worked together, neither of them had expressed any desire to be dishonest towards each other for any reason, for better or worse. And sometimes it was for the worst, but it never caused any longstanding friction between them.

Castiel had never lied, not once, and he believed it was the same with John. At least, he hoped it was so.

At 7:50am Castiel laid the book of identifying codes out in front of him, then stood at the window to watch the parking lot while he was on the phone. If John did show up, at least he would get advanced notice and could perhaps warn the agent.

A moment later his phone rang, startling him enough that he jumped away from the window and nearly fell over the obnoxious, huge fluffy chair that he had been unsuccesfully trying to get removed from his office for as long as he could remember. For some reason the furniture movers kept rescheduling over and over and over...he hadn't yet realized Gabriel was obstructing the effort all along as a practical joke that the whole office was in on.

"Good morning, John," Castiel answered, trying to sound completely normal.

"Ugh. Don't talk so loud."

"Sorry."

"My driver just dropped me off, but I forgot my badge. Can you come downstairs and swipe me in? I'm at the backdoor."

 _Shit. Shit. Shit._

"Sure. Be right there. Should I get an espresso going for you, too?"

"Yeah. Thanks."

Castiel hung up the phone and pressed the button to pre-heat the water, then made his way to the elevator with a pounding heart.

He should have lied.

 _God damn it._

 _/_

John flopped himself into Castiel's hated but extraordinarily comfortable chair, flinging an arm over his face to shield his sensitive eyes from the sun, while his chief strategist prepared the espresso for his boss without speaking. He didn't know what to say; in any case, there was no time. It was almost 8am.

He handed the cup to John, who blew on it for some time before asking, "You think he's going to call? Hope he's alright."

"I hope so. Listen, John, he...he wants to talk to me alone. I'm not sure he will agree to say a word if you're listening. Apparently he knows me and trusts me, but it doesn't appear he knows you."

"Or trusts me, apparently. That's fine. Don't tell him I'm on the line, then."

"I don't think that's a good idea."

"And I don't care. This isn't negotiable."

"John, please just-"

" _No._ Cas, please don't ask me such a thing ever again. I'm the goddamned leader of the party, in case you forgot."

Castiel clamped his mouth shut. John rarely pulled rank, but when he did, he meant business.

"And while I'm at it," John continued as he peered at Cas through half-closed eyelids, "I will nail your ass to the wall if you ever converse with an unverified asset again, do you hear me?"

"You are right on both counts, of course. My deepest apologies."

John leaned back and threw his arm over his eyes again. It was an overdue and well-deserved rebuke, and Castiel was relieved to get off so easy. It would have been far worse if John didn't have such a terrible hangover.

But Castiel still couldn't shake the deep feeling of dread that had darkened his thoughts since first hearing the agent's intel. Not that he believed the man. No, not at all. This was obviously the start of some darker, deeper threat perpetrated by Lucifer's own agents. It absolutely had to be, there was no question in his mind that this was a plot against John Winchester.

 _But what if it wasn't?_

At 7:59 Castiel lifted his cell phone, made sure John wasn't looking, and discreetly toggled the satellite connection to OFF.

Then he took a deep breath, said a prayer, and sat down to wait for the call that could never come.

/

TO BE CONTINUED


End file.
